Matthew D. Skipper

Advocating for Justice, Achieving Success, Building Trust
Matthew D. Skipper Photo
Matthew D. Skipper Managing Partner at Skipper Law, LLC

Legal Experience You Can Trust

Matthew D. Skipper is the managing partner of Skipper Law, LLC, a civil litigation firm located in Crofton, Maryland. Matt is one of the leading homeowners’ rights attorneys in not only Maryland but nationwide. He has been recognized as an expert witness in the field of community association law, and his cases have been featured in national publications. Prior to establishing Skipper Law, Matt founded the homeowners’ association/condominium practice group as an associate at a prior firm, a team dedicated to the representation of homeowners in claims against HOAs and condos. Matt has continued this work through Skipper Law, the only firm in Maryland known to focus on the representation of homeowners in community association disputes.

Matt is the lead personal injury attorney at Skipper Law, having recovered millions of dollars on behalf of those hurt by the negligence of others. As an experienced litigator, Matt works diligently to reach a favorable resolution, often without the need to file a lawsuit or step foot in court.

While most clients would rather resolve their cases without a trial, Matt has the experience needed to protect his client’s interests in court when litigation becomes inevitable. Matt has tried cases to verdict as lead counsel in the Circuit and District Courts of Maryland as well as the U.S. District Court for the District of Maryland.

While Matt has handled a variety of civil matters, he focuses his practice on the following areas:

Matt is also an experienced appellate litigator, having argued appeals in both appellate state courts, the Maryland Appellate Court and the Supreme Court of Maryland, as well as the federal U.S. Court of Appeals for the Fourth Circuit. Matt enjoys appellate work and has seen his appellate practice grow substantially.

Matt is admitted to practice law in Maryland state courts, the United States District Court for the District of Maryland, and the U.S. Court of Appeals for the Fourth Circuit located in Richmond, Virginia.

Matt, his wife, and their daughters live in Bowie, Maryland with their two chocolate labs. Matt enjoys playing basketball and softball, traveling, fishing, crabbing, hunting, and playing poker.

Recently, Matt was honored as a Leading Lawyer in HOA/Condominium law by What’s Up magazine, a recognition that highlights the top local lawyers. This distinguished honor is awarded based on peer nominations, showcasing his exceptional expertise in the field.

leading lawyer 2024-2025


  • JD, University of Maryland School of Law
  • BA, Grove City College in Grove City, PA


  • Maryland
  • U.S. District Court for the District of Maryland
  • U.S. Court of Appeals for the Fourth Circuit (Richmond, VA)


  • Anne Arundel County Bar Association
  • Maryland State Bar Association
  • Maryland Association for Justice
  • Greater Crofton Chamber of Commerce, Board of Directors Since 2013

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